Later, in Return to Hidden Cave, he Marvin, and Vinnie try to escape from jail by digging a tunnel with nothing but soup spoons. They begin their escape but are caught before they make it out of the guard fence. They are then transferred to a high security state penitentiary after said attempted escape. After arriving at the state penitentiary they meet a woman named Miranda. Miranda promises to get them out of jail just as long as they help in an attempt to steal highly classified computer chips. With no intention of actually helping Miranda, Simon agrees to the bargain. Once they escape from jail however, Simon, Marvin, and Vinnie are forced to help Miranda because she threatens to turn them in. Miranda then tells them to hide the computer chips in the Hidden Cave. Simon reluctantly agrees to the deal and he, Marvin, and Vinnie stow the computer chips in the cave. However, after Miranda realizes that the cave is supposed to be a large attraction at the Brenan Museum of Creation, she orders the three to go guard the computer chips until they can move them. While guarding the chips they are captured and returned to jail.

He appears again in Descent from Sandia Peak, where he, Marvin, and Vinnie are working at Sandia Peak National Park picking up garbage as part of their sentence. At the park he, Marvin, and Vinnie find themselves stuck in an tram with Mrs. Park, Ryan, and Mrs. Brenan. While on the tram Mrs. Park begins to have contractions. Simon, Marvin, and Vinnie begin to worry that Mrs. Park is going to have her baby on the tram, but Jonathan and Jessie fix the tram and Simon, Marvin, and Vinnie are forced to take Mrs. Park, Mrs. Brenan, Ryan, Jessie, and Jonathan to the hospital. After this excursion they are released and are not heard from again until The Journey Home.